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Winter Springs, FL Homes for Rent under $2,000

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    $1,489 - $2,261 per month

    Legends Winter Springs

    1 - 3 Beds

    440 Courtney Springs Cir, Winter Springs, FL 32708

    Legends Winter Springs effortlessly combines exceptional service with outstanding features to provide the ultimate living experience. Located near upscale shopping and entertainment, your home is minutes to Lake Jessup and the excitement of downtown Orlando. Enjoy the peaceful, relaxing atmosphere of Legends Winter Springs. Please call for an appointment today.

    440 Courtney Springs Cir, Winter Springs, FL 32708
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    $1,800 per month

    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    407 Sheoah Blvd Unit 9, Winter Springs, FL 32708

    This 3 bedroom, 2.5 bath condo is located in one of Winter Springs most desireable communities, THE HIGHLANDS! This unit features a large living and dining area, first floor guest half bath with a washer & dryer alcove, and large storage room. Back of property offers private views with no rear neighbors. The community amenities offer miles of walking trails, playground, park, tennis court and

    Helen Marshall BENSON MARSHALL LLC

    407 Sheoah Blvd Unit 9, Winter Springs, FL 32708
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    $1,595 - $2,790 per month

    RIZE at Winter Springs

    1 - 3 Beds

    150 Bear Springs Dr, Winter Springs, FL 32708

    RiZE at Winter Springs is a beautiful apartment community located in Winter Springs, Florida.All renderings, 3D Tours, Walkthrough Video Tours, Matterport Tours, and other multimedia materials are provided for illustrative and reference purposes only. Renderings are an artist’s conception and may not accurately represent the actual features, materials, finishes, or layout of any specific

    150 Bear Springs Dr, Winter Springs, FL 32708
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    $1,795 per month

    • 3 Beds
    • 1.5 Baths
    • 1,349 Sq Ft
    • House for Rent

    643 David St, Winter Springs, FL 32708

    Wonderfully updated 3-bedroom, 1.5-bath single family home in Winter Springs. Combined living and dining areas featuring a beautiful kitchen with breakfast bar, and stainless appliances. Large family room with washer and dryer closet, hook-ups only. Fully fenced backyard with storage shed. Conveniently located off 434 close to 17-92 and the Toll 417 for easy commuting and just a short drive to

    Christopher Gold WILSON MANAGEMENT GROUP

    643 David St, Winter Springs, FL 32708
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    $1,116 - $1,905 per month

    Avenues at Winter Springs

    1 - 3 Beds

    1 Laurel Oaks Dr, Winter Springs, FL 32708

    Experience resort-style living at The Avenues at Winter Springs! Our pet-friendly community offers spacious 1, 2, and 3-bedroom apartment homes with modern finishes and everyday conveniences.Enjoy amenities like a resort-style pool with sundeck, 24-hour fitness and wellness center, tennis court, playground, and leash-free pet park. Stay connected with 400 Mbps internet, and take advantage

    1 Laurel Oaks Dr, Winter Springs, FL 32708
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    $1,695 per month

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft
    • Townhouse for Rent

    603 Casa Park Ct N Unit h, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Charming 2-Bed, 2.5-Bath Townhome in Winter Springs with Screened Porch! Welcome to 603 Casa Park Ct. H, a cozy and well-maintained 2-bedroom, 2.5-bath townhome located just off Tuskawilla Rd in desirable Winter Springs. Offering 1,156 sq. ft. of living space, this home features a functional layout with an inside utility area and plenty of room for

    Jacob Hara TRANSCEND REALTY

    603 Casa Park Ct N Unit h, Winter Springs, FL 32708
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    $1,100 - $1,600 per month

    Mosswood

    Studio - 2 Beds

    101 Mosswood Cir, Winter Springs, FL 32708

    Welcome to Mosswood Apartments! At Mosswood, you'll find comfortable apartments with washer/dryer connections & extra storage. We're located just north of Orlando in Winter Springs, FL. Come home to our quiet residential setting & lake views that have easy access to I-417 and public transportation. Our single-story, villa-style East Winter Springs apartments feature private entrances and patios

    101 Mosswood Cir, Winter Springs, FL 32708
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    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft
    • Condo for Rent

    610 Casa Park Court H, Winter Springs, FL 32708

    CASA PARK VILLAS, this 2/1-unit features tile flooring, freshly painted, Close to Parks (Trotwood Park is across the street) and Recreation, schools, shopping and dining... Washer and Dryer hookups in unit. There is a nice open patio ,2 assigned parking spaces right in front of unit. The community has a nice POOL area and there is access to walking trails and biking nearby.

    Tony Martinez HOUSESTAR REALTY GROUP INC

    610 Casa Park Court H, Winter Springs, FL 32708
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    $1,545 - $2,401 per month

    The Eli Winter Springs

    1 - 3 Beds

    990 English Town Ln, Winter Springs, FL 32708

    Indulge in the luxury of living where others vacation at The Eli Winter Springs! Our community offers resort-class amenities and exceptional service to pamper residents. With a rich array of amenities, picturesque landscapes featuring swaying palm trees and tranquil waters, you can enjoy a paradise lifestyle. Conveniently located with easy access to 417, the Oviedo Marketplace, and major

    990 English Town Ln, Winter Springs, FL 32708
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    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,129 Sq Ft
    • Townhouse for Rent

    140 Mcleods Way, Winter Springs, FL 32708

    PRIME Location! Well maintained 2 bedroom, 2 bath Rental Townhome located in highly desired Jesup's Reserve. Walking distance to Winter Springs Town Center, Central Winds Park, Cross Seminole Bike Trail and just minutes to great shopping, dining and 417! CORNER Unit situated across the street from the Community Pool and a short walk to a community pond. Features included a Covered Front Porch,

    Emily Lemieux RE/MAX TOWN & COUNTRY REALTY

    140 Mcleods Way, Winter Springs, FL 32708
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    $1,334 - $2,175 per month

    Seville on the Green

    1 - 3 Beds

    300 Sheoah Blvd, Winter Springs, FL 32708

    Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature

    300 Sheoah Blvd, Winter Springs, FL 32708
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    $1,399 per month

    • 2 Beds
    • 2 Baths
    • 938 Sq Ft
    • Condo for Rent

    155 Cory Ln, Winter Springs, FL 32708

    Enjoy one month of free rent at the beginning of your lease! Welcome home! This fantastic 2-bedroom, 2-bath home is available for immediate move-in! Located conveniently in the desirable community of Winter Springs, this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features such as

    Steve Simpson 407 PROPERTIES

    155 Cory Ln, Winter Springs, FL 32708
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    $1,519 - $2,326 total monthly price

    Tuskawilla at Winter Springs

    1 - 3 Beds

    4545 Willa Creek Dr, Winter Springs, FL 32708

    We are now welcoming in-person, virtual and self-guided tours by appointment only. Please contact us today to schedule your appointment.Tuskawilla, Winter Springs, FL Apartments boast premier location great for both business and leisure. Located just minutes from SR417 and SR408, the Tuskawilla Apartments in Winter Springs are perfect for commuters all across Florida. Choose from a variety of

    4545 Willa Creek Dr, Winter Springs, FL 32708
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    $1,695 per month

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • Townhouse for Rent

    137 Garden Dr, Winter Springs, FL 32708

    This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for relaxing or unwinding after a busy day.

    Sylvia Pletka FLORIDA RENTAL TEAM

    137 Garden Dr, Winter Springs, FL 32708
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    $1,174 - $1,799 per month

    Moss Park

    1 - 4 Beds

    170 N Gardenridge Ct, Winter Springs, FL 32708

    Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located

    170 N Gardenridge Ct, Winter Springs, FL 32708
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    $1,695 per month

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • Townhouse for Rent

    133 Garden Dr, Winter Springs, FL 32708

    This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for relaxing or unwinding after a busy day.

    Sylvia Pletka FLORIDA RENTAL TEAM

    133 Garden Dr, Winter Springs, FL 32708
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    $1,845 per month

    • 3 Beds
    • 2 Baths
    • 1,091 Sq Ft
    • House for Rent

    306 San Gabriel St, Winter Springs, FL 32708

    Property Id: 6528763/2 Winter Springs Home - This cozy 3/2 single family home is priced to rent and won't be around for long. Text, email or apply online and schedule your tour today! This home features vaulted ceiling, lots of natural lighting, tiles throughout (no carpet!), and fenced in yard with a shed. Living room sliding glass doors open up to a private patio for sunning,

    306 San Gabriel St, Winter Springs, FL 32708
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    $1,600 per month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    70 Moree Loop Unit 63, Winter Springs, FL 32708

    Two story condominium in Winter Springs. The two bedroom, 1 and 1/2 bath unit is located in the Highlands community. Tile and laminate flooring, spacious layout, kitchen has a pass thru window to the dining area. Combo living/dining with sliding glass doors which offers natural sunlight and opens to an exterior patio. Two bedrooms, master full bath and laundry utility on the second floor.

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    70 Moree Loop Unit 63, Winter Springs, FL 32708
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    $1,800 total monthly price

    • 2 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Townhouse for Rent

    130 Kristi Ann Ct, Winter Springs, FL 32708

    Welcome home to this 2 bed, 1.5 bath townhouse in the heart of Winter Springs. You will be just minutes away from the Winter Springs Town Center, Great Seminole County Schools, Coffee Shops, Premium Gyms, Center Winds Park, and multiple conveniences nearby. The living room and patio offer ample space for relaxation and entertainment. Each bedroom is designed for functionality, with ceiling fans

    130 Kristi Ann Ct, Winter Springs, FL 32708
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    $1,500 per month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    407 Sheoah Blvd Unit 13, Winter Springs, FL 32708

    Excellent Location in the Highlands at Winter Springs. This two bedroom condo features a large living/dining room combo that opens out to the screen enclosed patio. Offering a quiet and peaceful yard space with no rear neighbors. The kitchen is spacious and features stainless appliances. Upstairs you will find two bedrooms along with a bathroom that is accessible directly off the primary as well

    Gina Jenkins WATSON REALTY CORP

    407 Sheoah Blvd Unit 13, Winter Springs, FL 32708
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    $1,815 - $3,050 per month

    Dwell Oviedo

    1 - 3 Beds

    500 Sugar Mill Rd, Oviedo, FL 32765

    500 Sugar Mill Rd, Oviedo, FL 32765
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    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,005 Sq Ft
    • House for Rent

    1373 Via Villa Nova, Winter Springs, FL 32708

    Beautiful/ immaculate 2 Bedroom/2 Bathroom House, Fully remodeled, 2 car Garage, in the Sunrise Subdivision, Ceramic tile floors, Appliances included are Refrigerator, Range, Dishwasher, Microwave oven. Washer/dryer hook ups, Close to Supermarkets and Seminole county Schools.

    Tony Martinez HOUSESTAR REALTY GROUP INC

    1373 Via Villa Nova, Winter Springs, FL 32708
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    $1,980 per month

    • 3 Beds
    • 2.5 Baths
    • 1,602 Sq Ft
    • Townhouse for Rent

    629 Pinebranch Cir, Winter Springs, FL 32708

    This must-see townhouse has an open kitchen with ceramic tile flooring, a snack bar, and all your essential appliances.The living room is flooded with natural light from the 2 sliding doors leading to the open patio with a pond where you can relax with a water fountain view shaded by cypress trees. All bedrooms are conveniently located upstairs, The master suite offers an oversize bathtub,

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    629 Pinebranch Cir, Winter Springs, FL 32708
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    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Apartment for Rent

    154 Tuskawilla Rd Unit 224, Winter Springs, FL 32708

    Wow! Talk about location! This apartment is situated in the lovely Winter Springs Town Center! The convenience of walking to Publix for shopping or going right across the street to Aldi is yours! The center has many shops, stores and restaurants ranging from Mexican to Italian, sushi or subs! There is also Spill(wine bar) that you can walk to and enjoy wine, beer, bites, and entertainment on some

    Deborah Morgan OPTIMA REAL ESTATE

    154 Tuskawilla Rd Unit 224, Winter Springs, FL 32708
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    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Apartment for Rent

    154 Tuskawilla Rd Unit 204, Winter Springs, FL 32708

    Wow! Talk about location! This apartment is situated in the lovely Winter Springs Town Center! The convenience of walking to Publix for shopping or going right across the street to Aldi is yours! The center has many shops, stores and restaurants ranging from Mexican to Italian, sushi or subs! There is also Spill(wine bar) that you can walk to and enjoy wine, beer, bites, and entertainment on some

    Deborah Morgan OPTIMA REAL ESTATE

    154 Tuskawilla Rd Unit 204, Winter Springs, FL 32708
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    $1,875 per month

    • 3 Beds
    • 2 Baths
    • 1,102 Sq Ft
    • House for Rent

    227 San Gabriel St, Winter Springs, FL 32708

    This charming 3-bedroom, 2-bathroom home located in the heart of Winter Springs, FL. The interior features a modern kitchen with stainless steel appliances, granite countertops, and ample cabinet space. The home offers tile and laminate wood flooring throughout, washer and dryer hookups inside the home, and a neutral color palette that complements any décor.

    Karla Arcelay TRUSTHOME PROPERTIES INC

    227 San Gabriel St, Winter Springs, FL 32708
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    $1,600 per month

    • 2 Beds
    • 2 Baths
    • 972 Sq Ft
    • Condo for Rent

    10 Sheoah Blvd Unit 8, Winter Springs, FL 32708

    Tastefully remodeled 2 Bed / 2 Bath very spacious condo for rent at The Highlands in Winter Springs. This is asecond-floor unit. Kitchen with granite countertop, stainless steel appliances and modern cabinetry. The Highlands is conveniently located off of SR 434 which makes for easy access to grocery stores, restaurants, schools, and major roadways such as 17-92, I-4, and the 417. The community

    Alejandro Echeverri The Keyes Company

    10 Sheoah Blvd Unit 8, Winter Springs, FL 32708
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    $1,795 per month

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • House for Rent

    506 San Gabriel Ct, Winter Springs, FL 32708

    Move In Special! Receive $250 OFF your first month of rent if approved and moving in by February 23rd!Welcome home to 506 San Gabriel Court, a charming 3 bedroom, 2 bath home featuring 1,187 square feet of living space. As you enter the home, you are welcomed into the main living area, featuring vaulted ceilings and plenty of natural light through the numerous windows and sliding glass

    Justin Recca INNOVATIVE REALTY, LLC

    506 San Gabriel Ct, Winter Springs, FL 32708
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    $1,695 per month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Townhouse for Rent

    208 Perth Ct Unit B, Winter Springs, FL 32708

    Highlights: 2 Car Garage | Spacious Backyard | Serene Patio | Community Pool | Nature Trails | BBQ Area Grills | Tennis Court | Community Playground | Picnic Area |Discover the vibrant charm of Winter Springs, nestled by the serene Lake Jesup and offering upscale living, diverse dining options, and a rich cultural scene. With pristine parks, top-notch schools, and annual festivities like

    Amy Johnston BELMONT REALTY

    208 Perth Ct Unit B, Winter Springs, FL 32708
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    $1,495 per month

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft
    • Property for Rent

    1954 Boat Club Rd, Oviedo, FL 32765

    Enjoy peaceful waterfront living in this 2-bedroom, 1-bath Mobile Home Duplex located on a canal off Lake Jessup. Recently updated, the home features newly renovated flooring, kitchen, and bathroom, offering a fresh and modern feel throughout. WATER INCLUDED! Relax and take in the serene water views right from your backyard, with direct canal access leading into Lake Jessup, perfect for enjoying

    Vicky Aeschilman LA ROSA REALTY CW PROPERTIES L

    1954 Boat Club Rd, Oviedo, FL 32765
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